Hydrochloric Acid → HCID 18916654, compound

HRID 1290667Notes

Reaction equation

[CH3:1][N:2]([CH3:46])[C:3]([C:5]1[CH:6]=[C:7]([CH:43]=[CH:44][CH:45]=1)[O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([N+:23]([O-])=O)=[C:11]([O:26][C:27]2[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:28]=2[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:10]=1)=[O:4].Cl>[Zn].C1COCC1>[CH3:1][N:2]([CH3:46])[C:3]([C:5]1[CH:6]=[C:7]([CH:43]=[CH:44][CH:45]=1)[O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([NH2:23])=[C:11]([O:26][C:27]2[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:28]=2[O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:10]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3-Dimethylaminocarbonylphenoxy)-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (H) (0.29 g, 0.47 mmol) and 0.1 g granular zinc were mixed with 10 mL THF and 1.0 mL 10% aqueous HCl. The reaction was heated at 80° C. for 90 minutes. The volatiles were evaporated. Saturated aqueous NaHCO3 was added and the solution extracted with ethyl acetate (300 ml). The organic layer was dried (Na2SO4) and evaporated to afford 0.27 g of 2-(3-dimethylaminocarbonylphenoxy)-4-benzylamino-5-amino-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (J).

Workup

customThe volatiles were evaporated
additionSaturated aqueous NaHCO3 was added
extractionthe solution extracted with ethyl acetate (300 ml)
dry with materialThe organic layer was dried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-0700e670f1e54113b89ed6f227630d9c
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753635

Reaction notes

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